Guanidin compound and process of making same.



Nrrnn STATES PATENT OFFICE.

ADOLF ISRAEL AND RICHARD KOTHE, OF ELBERFELD, GERMANY, ASSIGNORS TO FARBENFABRIKEN OF ELBERFELD (10., OF NEXV YORK, N. Y.

GUANIDIN COMPOUND AND PROCESS OF MAKING SAME.

SPECIFICATION forming part of Letters Patent N 0. 677,514, dated July 2, 1901.

Application filed February 20, 1901. Serial No. 48,167. (Specimens) T0 aZZ whom it may concern:

Be it known that We, ADOLF ISRAEL and RICHARD KOTHE,doctors of philosophy,chemists, (assignors to the FARBENFABRIKEN on ELBERFELD O0MPANY,of New York,) residing at Elberfeld, Germany, have invented a new and useful Improvement in New Guanidin Compounds and Processes of Making Same; and we hereby declare the following to be a clear and exact description of our invention. Our invention relates to the production of new guanidin derivatives having the following general formula:

on on SOHH HSCID-NH-(L;-NH-C,DHS SOQH! with ammonia or primary fatty or aromatic amins-such as methylamin, ethylamin, anilin, para -phenylenediamin, amidonaphthol, amidonaphthol sulfonic acid, or the like-in the presence of agents capable'of absorbing sulfureted hydrogen, such as lead oxid or the like. The said thio-urea compounds can be prepared, for instance, by treating with carbon bisulfid, sulfur, and alcohol such amidonaphthol sulfonic acids as do not contain the amide and the hydroxy group either in the so-called ortho position or in the so-called peri position. The new guanidin derivatives thus obtained are in the shape of the sodium salts grayish powders readily soluble in hot and soluble in cold water and being soluble with diflieulty in dilute mineral acids. They can be combined with diazo compounds, valuable azo dyestuffs being produced.

In carrying out our new process practically we can proceed as follows, the parts being by weight: 56.5 parts of the sodium salt of thiocarbonyl dioxydinaphthylamin disulfonic acid (obtained from beta -amid0-alpha -naphthol-betal -sulfonic acid) having the following formula:

are dissolved in from four hundred to five hundred parts of hot water. After the addition of from nine to ten parts of a twenty-percent. ammonia solution and from fifty to sixty parts of carefully-pulverized lead oxid the mixture thus obtained is heated in avessel provided with a reflux condenser by means of a Water-bath with continuous stirring. After a short time the color of the lead oxid begins to. grow black by the transformation into lead sulfid. The reaction is finished when the quantity of the latter no longer increases. Subsequently the reaction mixture is filtered, mixed with an excess of hydrochloric acid, and the guanidin derivative thus produced is precipitated from the filtrate by the addi tion of common salt, filtered 0E, and dried. It is then further purified by dissolving it in a sodium-carbonate solution and precipitating it again by the addition of common salt.

The new guanidin derivative having in a free state the following formula:

is, in the shape of the sodium salt, a grayish powder difficultly soluble in cold and soluble in hot water, soluble with difficulty in dilute mineral acids and in alcohol and being insoluble in ether.

The new guanidin derivative is capable of combining with one and likewise with two molecules of diazo compounds, thus furnish= ing valuable azo dyestufis.

IOO

The process proceeds in an analogous manner if instead of ammonia other of the abovementioned amins are used.

Having now described our invention and in what manner the same is to be performed,

what we claim as new, and desire to secure by Letters Patent, is

l. The process for producing newguanidin derivatives having the hereinbefore-defined generalformula:

OH on c H NH-C-NH-C H/ SOGH/ i H in \SO3H 1 R Y which process consists in heating the hereindefined thio-urea compounds of amidonaphthol sulfonic acids with amins in the presence of leadoxid, substantially as hereinbefore described.

2. The process for producing a new guanidin derivative having in a free state the following formula:

by first heating the herein-defined thio-urea compound of beta amido alpha naphthol- -beta;,-sulfonic acid with ammonia and lead with diazo compounds, valuable azo dyestufis being thus produced, substantially as hereinbefore described.

4. The herein-described new guanidin derivative of beta -amido-alpha -naphthol-beta;

sulfonic acid which, in the shape of the sodium salt, is a grayish powder difficultly soluble in cold and soluble in hotwater, soluble with difiicultyin dilute mineral acids and in alcohol, insoluble in ether and being capable of combining with one and likewise with two" molecules of diazo compounds,valuable azo dyestuffs being thus produced, substantially as hereinbefore described.

In testimony whereof we have signed our names in the presence of two subscribing wit ADOLF ISRAEL. RICHARD KOTHE. Witnessesi OTTO KoNIe, EMIL BLOMBERG. 

